John Hockaday spent much of his life in the Lytle Creek and Cajon Pass area, where he developed a deep familiarity with one of Southern California’s most important geographic corridors. He often described himself simply as “just an old construction worker who likes history,” but over time, that interest grew into a sustained, methodical study of the pass and its role as a gateway between the San Bernardino Valley and the Mojave Desert.
For more than four decades, Hockaday worked directly with the landscape. He walked abandoned road grades, traced alignments across hillsides and washes, compared historic maps with what remained on the ground, and photographed features that marked earlier phases of travel. His research was not confined to archives. It was built in the field, where physical evidence could be tested against historical records. He also collected oral histories from residents and families connected to the Route 66 and railroad eras, preserving local knowledge that might otherwise have been lost.
His work centers on Cajon Pass as a layered transportation corridor. Long before modern highways, the pass carried Native travel routes linking desert and valley systems. These pathways were later incorporated into the Old Spanish Trail and related trade routes. During the nineteenth century, the same corridor was used by Mormon migrants, emigrant parties, and freight operators moving goods between inland settlements and the coast. Wagon roads and toll roads formalized these routes, leaving behind cuts, benches, and grades that can still be seen today.
With the rise of automobile travel, Cajon Pass became part of the National Old Trails Road and later U.S. Route 66. Hockaday devoted particular attention to identifying the multiple alignments of Route 66 through the pass, distinguishing early grades from later improvements and documenting segments that have since been abandoned or erased. His work also extends into the transition to Interstate 15, showing how modern infrastructure continues to follow the same fundamental corridor established by earlier routes.
Working with his wife, Sandy Hockaday, he published the Trails & Tales of the Cajon Pass series. These books combine narrative history with maps, photographs, and firsthand accounts, offering one of the most complete modern records of travel through the pass. He also contributed to the National Park Service Old Spanish Trail mapping project, assisting in the identification of route segments and related features within the Cajon Pass region.
Among Southern California historians, Hockaday is best understood as a field historian. His approach emphasizes direct observation and verification, using the landscape itself as primary evidence. Rather than relying solely on written sources, he worked to confirm where routes actually ran, how they shifted over time, and what physical traces remained. This method allowed him to document not only the idea of a route but also its actual position on the ground.
His work helped preserve knowledge of early wagon road alignments, Route 66 grades, Camp Cajon, and the early automobile travel era, and the broader development of rail and highway systems through the pass. As development, erosion, and time continue to erase older features, that record has become increasingly important.
Cajon Pass has always functioned as a gateway, shaped by geography and repeatedly reused by successive generations. Hockaday’s work clearly demonstrates continuity. By documenting the corridor at ground level, he showed how each layer of travel builds on the last, forming a continuous thread from Native footpaths to modern interstate highways.